Pack your bags: this is The Hamptons like only the locals know it.

By Laura Begley Bloom
June 11, 2012
Insider's Guide to the Hamptons
Credit: Theo Morrison

On my first visit to the Hamptons some 20 years ago, I stayed with friends at a sprawling rental in Southampton. We hired a now-defunct taxi service (Mercedes-Benzes, of course) to take us to overpriced restaurants and red-rope clubs. It was exactly how I’d pictured Long Island’s South Fork—a bit pretentious for my tastes.

But there was something about this beachy New York destination that spoke to me: the dramatic dunes; the shingled windmills; and that famous light that has attracted artists as varied as Jackson Pollock and Winslow Homer. So I kept coming back, renting houses with friends and staying at inns from Amagansett to Sag Harbor, East Hampton to Montauk. Eventually, I bought a cottage in Amagansett with my husband (whom I met at a bonfire on Atlantic Beach).

Over the years, I’ve discovered a very different side to this coastal getaway. My Hamptons is all about low-key seafood shacks, quirky antiques shops, and placid bays that are perfect for beachcombing. Sure, you might run into Paul McCartney at the local café or spot Gwyneth Paltrow’s kids selling lemonade at a makeshift stand—but that is just evidence of the Hamptons’ many faces.

Read on for my highly selective guide.

Where to Stay

The Classics

The Maidstone Arms, a sprawling Greek Revival inn overlooking the town pond, has been the place to stay in East Hampton for generations. A much-welcome overhaul gave it an offbeat new name, c/o The Maidstone, and a Swedish design sensibility; most of the 16 rooms and three cottages are inspired by famous Scandinavians (Arne Jacobsen, Hans Christian Andersen, even Edvard Munch). Just down the street behind an ivy-covered façade is the Baker House 1650, with five Arts and Crafts–style rooms and two lovely outdoor pools. The American Hotel, a red-brick Victorian in the center of Sag Harbor, stands in stark contrast: it hasn’t changed much since 1846. And that’s just how guests like it, with its faded elegance, backgammon tables in the lobby, and a bartender who will soon know your name. Another popular dowager: Southampton’s 152-year-old A Butler’s Manor, which is surrounded by lush English gardens. Each of the five individually decorated rooms is named after an estate where co-owner Christopher Allen—a former butler—once worked.

The New Guard

By far the most luxurious hotel in the area is Amagansett’s Inn at Windmill Lane, briefly known as the Reform Club (rumor has it the owners changed the name because it sounded like a rehab center). It is worth the splurge: the seven suites have wood-burning fireplaces; each of the three cottages also has its own gym and steam room. In Montauk, Ruschmeyer’s is a summer camp for grown-ups. Think cabins clustered around a decorative tepee, bingo nights, Ping-Pong, and a bar in an oversize sandbox. Solé East Resort is set in a Tudor-style house, with 61 whitewashed rooms; an allée of bamboo leads to eight garden cabanas out back. On Shelter Island, La Maison Blanche, named after a hotel in St.-Tropez, channels the south of France: pétanque courts, a Gallic brasserie, and an authentic boulangerie.

Waterfront Hotels

There are surprisingly few good hotels on the water in the Hamptons, but the rooms are clean and simple at Amagansett’s White Sands Resort Hotel, smack on a spectacular Atlantic beach. Worth booking for the ocean views alone is Montauk’s hillside Panoramic View Resort & Residences; the pastel bathrooms and kitchenettes betray its previous life as a 1950’s motel. On a small islet, the Montauk Yacht Club Resort & Marina has a scaled-down replica of the town’s famous lighthouse, not to mention three pools, four tennis courts, a spa, and a marina. For a dose of glamour by the sea, check out Shelter Island’s Sunset Beach, which has a vibrant social scene, its own brand of rosé, and spectacular sunsets (as the name would suggest). Last summer, owner André Balazs introduced StndAir, a bright red seaplane from Manhattan to East Hampton that sometimes lands in the cove in front of the hotel. One-way rates start at $595.

Where to Eat

The Hot Dish

Foodies flock to Shelter Island’s Vine Street Café for crisp calamari salad and miso salmon in a simple space with high, beamed ceilings. In the tiny town of Water Mill, Bistro Été serves meticulously prepared French Mediterranean cuisine in a 1670 stagecoach house. In Bridgehampton, opt for Almond for the best seasonal and local fare. When in Amagansett, for a simple yet delectable wine and cheese night, take out from Cavaniola, or head to La Fondita for traditional Mexican street food. It’s no surprise that Gabby Karan De Felice’s Tutto Il Giorno is so stylish, considering her mother is Donna Karan; the lusty dishes range from branzino al forno to house-made pappardelle. The restaurant has two locations: Sag Harbor (the original) and Southampton. In Montauk, two places are adding to the town’s new culinary cred: Navy Beach, a former surfer’s bar right on the sand with a great menu of ceviches, and the waterfront Crow’s Nest, a rustic-chic spot from hipster hotelier Sean MacPherson.

Farm (and Ocean) to Table

Despite all the changes, the South Fork is still home to fishermen who make a living offshore and family farms that have been around for generations—providing ample resources for chefs such as Joe Isidori at Bridgehampton’s Southfork Kitchen. He has gained a following for his unswerving commitment to sustainable seafood, fresh produce, and Long Island wines. The most coveted reservation continues to be East Hampton’s 24-year-old Nick & Toni’s, which is a who’s who: Howard Stern, Lou Reed, and Naomi Watts, just to name a few. Chef Joseph Realmuto sources from the best local purveyors for such dishes as dandelion greens and pork-belly croutons in a white-anchovy vinaigrette. In Montauk, Jennifer Meadows, the adorable chef-owner of Fishbar, is so friendly with the fishermen that she radios them when they’re at sea to check out what they’ve caught. Her second venue, Bliss Kitchen isan eclectic takeaway with a fleet of taco-delivery bikes buzzing around town. One of the toughest tables to get in Montauk is at Dave’s Grill. In-the-know diners start dialing at 4:15 p.m.—when the reservation line opens—to sample hearty cioppino and onion-and-potato-crusted flounder.

Seafood Shacks

There’s nothing like a platter of good old fried oysters or steamers by the sea. At Canal Café, tucked into a Hampton Bays marina, you’ll get one of the most generous lobster rolls around—plus great water views and salty air in your hair. In a weathered cottage on Sag Harbor’s wharf, groupies line up at the Dock House for the clam chowder and steamed lobsters; the live specimens are kept in an antique bathtub next to the front door. You can’t get a better endorsement than chef Bobby Flay, who has been spotted at Bostwick’s Chowder House, East Hampton’s destination for shoreside favorites. On the stretch between Montauk and Amagansett, look for the yellow-and-white-striped umbrellas: the open-air Clam Bar serves simple seafood (I prefer it to the more famous Lunch, a.k.a. the Lobster Roll, down the street). Bring a bottle of rosé to Duryea’s Lobster Deck, set on a rocky Montauk outcropping and renowned for its well-priced lobster. Just be prepared for a long wait.

Best Breakfasts

Almost as social as dinner, breakfast is an institution in these parts. So local residents were devastated when the decades-old Fairway Restaurant, at Sagaponack’s Poxabogue Golf Center, lost its lease in 2010. After a heated battle with the town, it soon reopened, looking as retro as ever and once again supplying happy Hamptonites with no-fuss bacon and eggs. Another unassuming cult spot in a 1959 Hampton Bays motel is the Hampton Maid, known for its fluffy omelettes and decadent French toast. A few notches up on the culinary barometer is Estia’s Little Kitchen, a modern-Mexican roadhouse in Bridgehampton where regular Alec Baldwin has a menu item named after him: the egg-white “Big Al’s Burrito.” In Amagansett, the cheddar-scallion scones alone are worth the wait at Mary’s Marvelous, a low-key neighborhood haunt that also makes addictive cookies and sweets. You’ll also encounter lines outside Montauk’s Mr. John’s Pancake House for such indulgent combinations as the “ET” (chocolate and peanut-butter chips) and the “sabre” (coconut-filled and topped with coconut syrup). On a health kick? Follow the surf crowd to Joni’s for whole-wheat breakfast burritos and chai lattes.

Where to Shop

Farm Stands and Wineries

The surrounding landscape used to be covered with potato fields; now heirloom tomatoes, baby beets, and wine grapes are some of the crops of choice. And that means a plethora of places to find the local bounty. When Rocco DiSpirito wants to make Mexican corn with chili mayo, he stocks up on the ingredients at Water Mill’s Green Thumb Organic Farm. After buying cheeses, fruit pies, and grass-fed beef at Bridgehampton’s Fairview Farm at Mecox, make your way through the winding corn maze. Set under huge chestnut trees in East Hampton, Round Swamp Farm sells everything from guacamole to chocolate-chip muffins. Perhaps the most atmospheric stand is Vicki’s Veggies, a bright red gem in Amagansett for just-harvested corn and incredible pies baked by Vicki herself (regulars are allowed access to the pick-your-own-herb garden out back). And of course, a trip to Long Island wouldn’t be complete without a wine tasting. My choices: Bridgehampton’s Channing Daughters Winery, where the vineyards are dotted with the owner’s sculpture collection, and Sagaponack’s Wölffer Estate Vineyard, which hosts free Friday jazz at sunset, overlooking the vines.

Clothing and More

Making a sartorial statement here means standing out from the pack, so I seek out boutiques with an individual point of view. In an Amagansett cottage, Brazilian-born Claudja Bicalho and her Australian husband, Mark Wilson, run Lazy Point, full of sexy-but-sophisticated clothes and jewelry found during their world travels. Down the street, the colorful Pink Chicken outfits pint-size beachgoers in floral dresses and tunics (there are some matching mom looks, too). In a converted Wainscott diner, Tomas Maier (you know him as the creative director of Bottega Veneta) sells some of the most arresting (and form-flattering) swimwear around. At Jennifer Miller Jewelry in Southampton and East Hampton, the baubles are perfect for a glittering poolside party. Among East Hampton’s other enticing one-off boutiques is the Monogram Shop: love the personalized totes and the cocktail napkins emblazoned with cheeky phrases like forced family fun and have you seen my contractor? The French-influenced *share with...Montauk is the location for the authentic striped fishermen’s tops that everyone is wearing lately. Elizabeth Donnarumma left her career as a brand manager to open Quogue’s Homespun; there’s a grab bag of summery finds, from sea-themed linens to silver sailcloth beach bags. Speaking of sailcloth, all of Shelter Island’s Shelter Ego is wrapped in it; the breezy shop stocks both the fashionable (earrings woven from golden thread) and the eccentric, like the wooden pig bookends my mother-in-law bought for my house.


Thanks to wealthy homeowners who have money to burn (and decorators to help burn it), the Hamptons has its share of wildly overpriced antiques stores. But there are a few reasonable gems, if you know where to look. My top source is Sag Harbor’s weekends-only Sage Street Antiques. Get there when it opens: owner Eliza Werner’s selection of etched glassware, Art Deco lamps, nautical relics, and white-painted dressers moves fast. Nearby, the highly personalized Ruby Beets mixes in new treasures such as handblown glass lamps with the antiques. On Shelter Island, Marika’s Eclectic Boutique looks like a flea market: Heywood-Wakefield tables, bamboo bar carts, and iron garden furniture spill out into the front yard. Similarly, you never know what you’ll uncover at Collette Home, an interiors consignment shop in Southampton. On a recent visit, I spied a vintage wooden racing car and a set of metal Navy chairs. (Collette also has sister shops in Southampton and Sag Harbor for secondhand designer clothes.) Set in a Bridgehampton farmhouse, Laurin Copen Antiques is more refined, with its Sweden-meets–South Fork sensibility. On the other end of the spectrum is Melet Mercantile, in an unassuming Montauk garage where Bob Melet—former director of vintage buying at Ralph Lauren—displays used surfboards, 1970’s rock concert T-shirts, and other offbeat discoveries.

What to Do

Historic Houses

Artists have long made the Hamptons a studio by the sea. Perhaps two of the most famous residents were Jackson Pollock and his wife, Lee Krasner; at the Pollock-Krasner House & Study Center, in East Hampton’s Springs area, you can tour their 1879 residence and studio, complete with paint splotches on the floor. Not to miss on the other side of East Hampton: LongHouse Reserve, founded by textile designer and crafts expert Jack Lenor Larsen. Works by artists Willem de Kooning and Sol LeWitt dot the acres upon acres of gardens.


Another top East Hampton destination is Guild Hall, a center for visual and performing arts. Board member Alec Baldwin often hosts readings and theater performances; this August, the museum will be turned over to Eric Fischl’s beach paintings. In Southampton, the well-regarded Parrish Art Museum, established in 1897, is about to move its collection of 19th-, 20th-, and 21st-century American art into a dazzling new Water Mill space designed by Herzog & de Meuron. Run by the Dia Art Foundation, Bridgehampton’s Dan Flavin Art Institute displays the artist’s light sculptures in a former firehouse and church.


One of the joys of a visit here is getting out into the fresh air. When designer Tory Burch wanted her kids to have surfing lessons, she hired Flying Point Surf School, in Southampton, which also helps adults learn to ride the waves. Not feeling quite as intrepid? Girls can try their hand at the newly popular sport of stand-up paddleboarding with Paddle Diva. (Guys can get in on the action at Wainscott’s Main Beach Surf & Sport.) There are plenty of bays for kayaking; one of my favorites is the serenely beautiful Accabonac Harbor. Rent kayaks from East Hampton’s picture-perfect Springs General Store. A sportfishing capital, Montauk has a marina that is crowded with charter boats. One of the top guides is expert angler and photographer Jim Levison, who will take you on saltwater fly-fishing expeditions.

Nature Trails

Don’t miss the Hither Hills State Park Walking Dunes Trail: hidden between Amagansett and Montauk, these shifting mountains of sand move several feet a year. Near Sag Harbor, the birds eat right out of your hand at the Elizabeth A. Morton National Wildlife Refuge. On Shelter Island, the Nature Conservancy’s Mashomack Preserve offers hiking trails through various ecosystems and past kettle holes formed by glaciers during the Ice Age.

After Dark

The nightlife scene is a mixed bag: I usually prefer walking on a moonlit beach to standing in line for a club. But when I’m feeling social, a few places are worth the effort. Among them are Amagansett’s Stephen Talkhouse, which hosts acts like Jimmy Buffett. At the Capri, in Southampton, the poolside Bathing Club wakes up when the DJ’s start spinning. In Montauk, the buzzing Surf Lodge had come under criticism for its crowds of late-night revelers: the new management promises a more mellow scene, so you can peacefully sip mojitos by the waterfront fire pit. And the season wouldn’t be complete without the Fourth of July party at Rick’s Crabby Cowboy Café & Marina, in Montauk, a down-and-dirty seafood joint that comes alive one night of the year. Filled with celebs and locals, it’s a can’t-miss affair that defines summer in the Hamptons.

Getting There

It can take 90 minutes to four hours to drive to the Hamptons from New York City. You can also go by Long Island Rail Road or Jitney, a luxury bus service. For a speedier arrival, there’s the seaplane StndAir. Once there, it’s a good idea to have a car, but be aware that many of the beaches have parking regulations; most hotels will provide a pass.

Recommendations By Region:


Stay at Inn at Windmill Lane and White Sands Resort Hotel.

Eat at Amagansett Seafood Store, Clam Bar, and Mary’s Marvelous.

Shop at Lazypoint, Pink Chicken, and Vicki’s Veggies.

Go: Hither Hills State Park Walking Dunes Trail, Stephen Talkhouse.


Eat at Estia’s Little Kitchen, Southfork Kitchen, Topping Rose House.

Shop at Fairview Farm at Mecox and Laurin Copen Antiques.

Go: Channing Daughters Winery, Dan Flavin Art Institute.

East Hampton

Stay at Baker House 1650, The Maidstone.

Eat at Bostwick’s Chowder House, Lucy’s Whey, and Nick & Toni’s.

Shop at Jennifer Miller Jewelry, Monogram Shop, and Round Swamp Farm.

Go: Guild Hall, LongHouse Reserve,Paddle Diva, Pollock-Krasner House, and Springs General Store.

Hampton Bays

Eat at Canal Café and Hampton Maid.


Stay at Montauk Yacht Club, Panoramic View Resort, Ruschmeyer’s, and Solé East Resort.

Eat at Bliss Kitchen, Crow’s Nest, Dave’s Grill, Ditch Witch, Duryea’s Lobster Deck, Fishbar, Joni’s, Mr. John’s Pancake House, Navy Beach, and Rick’s Crabby Cowboy Café.

Shop at Melet Mercantile.

Go: Jim Levison and Surf Lodge.


Stay at Inn at Quogue.

Shop at Homespun.


Eat at Fairway Restaurant and Sagg Store.

Sag Harbor

Stay at American Hotel.

Eat at Dock House and Tutto Il Giorno.

Shop at Ruby Beets and Sage Street Antiques.

Go: Elizabeth A. Morton National Wildlife Refuge.

Shelter Island

Stay at La Maison Blanche and Sunset Beach.

Eat at Bob’s Fish Market and Vine Street Café.

Shop at Marika’s Eclectic Boutique and Shelterego.

Go: The Nature Conservancy’s Mashomack Preserve.


Stay at A Butler’s Manor.

Eat at Blue Duck Bakery Café and Tutto Il Giorno.

Shop at Collette Home and Jennifer Miller Jewelry.

Go: Capri, Flying Point Surf School, and Parrish Art Museum.


Shop at Tomas Maier.

Go: Main Beach Surf & Sport.

Water Mill

Eat at Bistro Été.

Shop at Green Thumb Organic Farm.


Eat at Beach Bakery Café.

So where are the Hamptons? Its boundaries are often debated, but here’s a snapshot of the region, from west to east:

Westhampton: The gateway to the region, with a quaint town center and miles of beaches.

Quogue: A quiet, blink-and-you’ll-miss-it village; gracious old houses line the tree-shaded streets.

Hampton Bays: Has a distinctly nautical feel; boats almost outnumber residents.

Southampton: Manicured lawns and mansions behind hedges. Old money is never far away.

Water Mill: A small town that’s really big on food. I’ve nicknamed it Water Meal.

Bridgehampton: Antiques shops and summer polo tournaments—need I say more?

Sagaponack: Rolling dunes and plenty of farm stands for locavores.

Wainscott: Barely a blip on the map, with some of the most expensive real estate in the nation.

East Hampton: The town that has it all: shops, restaurants, beaches, celebs.

Amagansett: Best of the beach and bay; some pretty good live music, too.

Montauk: Newly hip fishing town at the tip of the South Fork that still retains its old-fashioned charms.

Sag Harbor: Onetime whaling port turned artists’ enclave with year-round appeal.

Shelter Island: A secluded retreat accessible by ferry or boat.

Here, a few top strands—and where to pick up lunch before you hit the shore.

Atlantic Avenue Beach, Amagansett: Also known as Asparagus Beach.

The Bite: Amagansett Seafood Store: Just-off-the-boat scallop ceviche.

Coopers Beach, Southampton: Great for kids, plus summer concerts on the sand.

The Bite: Blue Duck Bakery Café: Ham and more on freshly baked artisanal bread.

Ditch Plains, Montauk: The area’s surfing mecca.

The Bite: Ditch Witch: A food truck with addictive Jamaican patties.

Main Beach, East Hampton: Complete with beach-chair and umbrella rentals.

The Bite: Lucy’s Whey: Chic fromagerie for takeaway cheese plates.

Sagg Main Beach, Sagaponack: White sands and volleyball matches.

The Bite: Sagg Store: Meatloaf sandwiches that have a loyal following.

Shell Beach, Shelter Island: Excellent shell collecting.

The Bite: Bob’s Fish Market: Lobster rolls and clambakes to go.

Westhampton Dunes: A narrow Atlantic barrier island.

The Bite: Beach Bakery Café: Classics like tuna sandwiches and peach pie.

Dock House

Perched on a grassy plateau high above the waterfront, this 19th-century stone residence with sweeping Table Bay views was once the Harbormaster’s Mansion. After a major 2008 refurb, it opened as a glamorous six-room boutique hotel, decorated throughout with ornate French mirrors, crystal chandeliers, contemporary charcoal artwork, and luxurious antiques (like a Persian winged bed), set against a calming taupe palette. Upon your arrival, friendly linen-clad butlers—there are three of them—will gladly unpack your suitcases while you retire to the spa Tylarium (a sauna/steam room combo) or the gym with its Table Mountain–facing treadmills. In the afternoons, culinary treats like crayfish wraps are offered to guests lounging around the elegant (heated) swimming pool.

Room to Book: Room 5 has the largest private balcony, with a panoramic harbor view, perfect for private breakfasts or afternoon lounging.


After riding the morning waves, everyone gathers for breakfast burritos and chai lattes at Joni's.

Share with...Montauk

Striped Breton sailor tops hang from driftwood displays at this fair-trade- and organic-focused shop. Its owner, Joelle Klein, used to be a designer for Calypso Christianne Celle.

Montauk Yacht Club

The 80-year old island staple, where Charles Lindbergh once visited, gave its 107 rooms a multimillion dollar overhaul in 2009. The property has a scaled-down replica of the town’s famous lighthouse, not to mention three pools, four tennis courts, a spa, and a marina.

Solé East Resort

The low-key Tudor-style hotel has beachy accents like sisal carpets and wood-burning fireplaces.

Surf Lodge

Owned by a team of New York City club impresarios, the Surf Lodge made a splash when it opened its 32-waterfront rooms on Fort Pond in the summer of 2008. The property includes a tiny Tracy Feith shop filled with caftans, a restaurant helmed by Top Chef star Sam Talbot, surf movies on rotation 24/7 in the lobby, and an open-air deck that doubles as the Hamptons' hottest nightspot. The property had come under criticism for its crowds of late-night revelers: the new management promises a more mellow scene, so you can peacefully sip mojitos by the waterfront fire pit.

Duryea’s Lobster Deck

Bring a bottle of rosé to Duryea’s Lobster Deck, set on a rocky Montauk outcropping and renowned for its well-priced lobster. Just be prepared for a long wait.

Nick & Toni's

The most coveted reservation continues to be East Hampton’s 24-year-old Nick & Toni’s, which is a who’s who: Howard Stern, Lou Reed, and Naomi Watts, just to name a few. Chef Joseph Realmuto sources from the best local purveyors for such dishes as dandelion greens and pork-belly croutons in a white-anchovy vinaigrette. Get a table in the garden.

Vine Street Café

Foodies flock to Shelter Island’s Vine Street Caféfor crisp calamari salad and miso salmon in a simple space with high, beamed ceilings.

Wölffer Estate Vineyard

This inviting, state-of-the-art winery with award-winning wines hosts free Friday jazz at sunset, overlooking the vines.

Sunset Beach

In the late 1990s, hotelier André Balazs put his fashionable stamp on New York’s tranquil Shelter Island by turning a vintage motel into a buzz-worthy inn. More than 10 years later, the property has managed to retain its chic sensibility without disrupting the island’s laid-back vibe. What makes this hotel a worthy spot when compared to properties in the nearby Hamptons? Its location on Crescent Beach, one of the area’s top spots for watching the sunset. Inside, 20 white-on-white rooms are refreshing and simple, punctuated by cheery bursts of orange and yellow. All have spacious private decks that face the sea.

LongHouse Reserve

Stroll the sculpture gardens at the 16-acre arts space, ounded by textile designer and crafts expert Jack Lenor Larsen. Works by artists like Willem de Kooning, Sol LeWitt, Yoko Ono and Dale Chihuly dot the acres upon acres of gardens. .

White Sands Resort Hotel

Hidden in the dunes beyond the center of Amagansett, the property isn’t the height of glamour, but it has steps leading right onto a private beach.